When Conrad Black’s years-long odyssey through the U.S. legal system finally concludes this weekend with his release from a Florida prison, he will be greeted back in Toronto by warm friends and eager potential employers. But serious troubles remain that could leave him emotionally and financially depleted, including an ailing wife and a $70-million bill from the U.S. Internal Revenue Service.

And although he said last summer that he also expected to resume his life in the United Kingdom, where he has a seat in the House of Lords, other felons who have attempted to return to that august institution, including the author Jeffrey Archer, have been shamed into leaving.

At the moment, Lord Black does not even know where he will end up after his release. While he hopes to travel directly to Toronto when he is sprung on Friday or Saturday from Coleman Correctional Complex, near Orlando, U.S. authorities may choose to deport him to the U.K., the country of his most recent – albeit expired – passport.

If that happens, his next move would likely be a flight to Toronto.

The former newspaper titan has been granted a one-year temporary resident permit, which has outraged some Canadians for its appearance of special treatment by the Department of Citizenship and Immigration.

“Many of us will welcome him with open arms.” said Michael Levine, his friend and agent who negotiated the sale of Lord Black’s bestselling memoir,
A Matter of Principle. “Whatever the truth of the different positions in relation to the events of some years ago, I think the dignity and grace and courage and intelligence that he’s exhibited over the past several difficult months has impressed a lot of people.”

Lord Black exhibited those traits floridly and on a regular basis during his time in prison, through blog posts and newspaper columns, including a regular perch in the National Post. “I flourished as a writer, both in books, and magazines and newspapers, so I’ll stick with that,” he said during an interview with The Globe and Mail before he returned to prison for the final eight-month chunk of the 37 months he served.

Even his nemesis David Radler, who co-founded the Hollinger newspaper group in the 1960s before becoming the prosecution’s star witness against Lord Black, said he would like to meet his old friend again. “I'm happy to. What did we have? Forty-odd years together?”

Lord Black’s memoir is nominated for the National Business Book Award, which will be presented later this month at the Ritz-Carlton Toronto hotel.

Paul Godfrey, the CEO and president of the Post’s parent company, Postmedia, said Lord Black would continue to be welcome in its pages. “I’m sure that as an active businessman before this interruption, he’s probably thought about his future and what he wants to do,” said Mr. Godfrey. “But we do hope he continues to be a columnist.”

“He’s one of our best read – whether people like him or dislike him, they read him,” Mr. Godfrey said. “In the time he was away, I don’t think he missed a beat. If he’s not in for a week, which is rare, we get calls asking why.”

And Lord Black has many different options open to him. “I have enough money and connections to get into investing,” he noted during the interview. “And especially now, the macroeconomic managers have made such a horrible mess of things, it’s not hard to make money if you know what you’re doing.”

Still, numerous clouds hang over Lord Black’s future. Two years ago, the IRS hit him with notices alleging he failed to pay taxes on a variety of payments for services. His legal team has argued the IRS claims are based on the same evidence that formed the initial basis of his prosecution for fraud, which was later largely dismissed.

In pleading for a shorter sentence last year, Lord Black told U.S. authorities that the health of his wife, Barbara Amiel, precluded her living in a warm climate.

Not all of Lord Black’s legal tussles have him on the defensive. He has an outstanding libel suit against the British author Tom Bower arising from Conrad and Lady Black: Dancing on the Edge, which infuriated Lord Black with its snarky descriptions of the mogul. The $2.5-million suit was frozen during Lord Black’s time in prison, but although British libel laws are friendlier to plaintiffs than Canada’s, he may find pursuing the case to be more trouble than it is worth. On Wednesday, Mr. Bower put the matter plainly: “How can a convicted fraudster find a jury who will say that his reputation has been damaged by a book that says he’s a fraudster?”

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